6-Aminohexanoic Acid → 4-carboxy-N-(5-carboxypentyl)phthalimide

HRID 992217Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([OH:3])=[O:2].[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]>>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([OH:3])=[O:2]

Participants

Reactant 2

HCID 5646-Aminohexanoic Acid

HCID 11089Trimellitic anhydride

Product 1

HCID 17265614-carboxy-N-(5-carboxypentyl)phthalimideYield 85%

Procedure

4-carboxyphthalic anhydride (1.0 g, 0.0052 mol) and 6-aminohexanoic acid (0.68 g, 0.0052 mol) were refluxed as above overnight. Crystallisation of the product from EtOH yielded 1.35 g (85%) of 104 as a white solid: mp=202-204° C.; Rf0.80 (A): Rf0.84 (B): Rf0.47 (D): IR (cm−1): 2800-3250 (OH), 3103 (C═CH), 2675 (C—H), 1769 (C═O), 1709 (bs, C═O), 1625 (C═C), 1485 (C═C), 1403(C—O), 1303 (C—O), 730 (C═CH); MS m/z (rel intensity) 305 (16), 304 (100).

Workup

customCrystallisation of the product from EtOH

Sources & evidence

ORD record: ord-aa8b4c006106476d8952000c867c3362
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06468990B1

Reaction notes

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